1-[P,ALPHA-DIPHENYLBENZYL]IMIDAZOLE
bifonazole
CAS: 60628-96-8
Molecular Formula: C22H18N2
1-[P,ALPHA-DIPHENYLBENZYL]IMIDAZOLE - Names and Identifiers
| Name | bifonazole |
| Synonyms | bifonazol bifonazole trifonazole Bifonazole Impurity Biphenylylbenzylazole 1-(p,a-Diphenylbenzyl)imidazole Bifonazole for system suitability 1[4,ALPHA-DIPHENYLBENZYL]-IMIDAZOLE 1-[P,ALPHA-DIPHENYLBENZYL]IMIDAZOLE 1-[phenyl-(4-phenylphenyl)-methyl]imidazole 1-[biphenyl-4-yl(phenyl)methyl]-1H-imidazole |
| CAS | 60628-96-8 |
| EINECS | 262-336-6 |
| InChI | InChI=1/C22H18N2/c1-3-7-18(8-4-1)19-11-13-21(14-12-19)22(24-16-15-23-17-24)20-9-5-2-6-10-20/h1-17,22H |
1-[P,ALPHA-DIPHENYLBENZYL]IMIDAZOLE - Physico-chemical Properties
| Molecular Formula | C22H18N2 |
| Molar Mass | 310.4 |
| Density | 1.1150 (rough estimate) |
| Melting Point | 142℃ |
| Boling Point | 440.55°C (rough estimate) |
| Flash Point | 251.2°C |
| Solubility | Solubility in water when soluble in alcohol, dimethylformamide and dimethylsulfoxide Ph = 6:<0.1mg/100ml. Stable in aqueous solutions with Ph = 1~12. |
| Vapor Presure | 2.46E-09mmHg at 25°C |
| Appearance | White crystal or crystalline powder |
| Color | white to off-white |
| Merck | 14,1213 |
| pKa | 6.55±0.22(Predicted) |
| Storage Condition | Sealed in dry,Room Temperature |
| Sensitive | Easy to absorb moisture and sensitive to air |
| Refractive Index | 1.7620 (estimate) |
| MDL | MFCD00865567 |
| Physical and Chemical Properties | Crystallization from acetonitrile, melting point 142 °c. Strong lipophilic. Soluble in alcohol, dimethyl formamide, dimethyl sulfoxide. Solubility in water at Ph = 6:<0.1mg/100ml. Stable in aqueous solution of Ph = 1~12. Acute toxicity. Male mice, rats (mg/kg):2629,2854 oral. |
| Use | Imidazoles new antifungal drugs for external use in the treatment of various dermatophytes, such as Tinea corporis, tinea cruris, tinea pedis and tinea pedis. |
1-[P,ALPHA-DIPHENYLBENZYL]IMIDAZOLE - Risk and Safety
| Hazard Symbols | Xn - Harmful |
| Risk Codes | 22 - Harmful if swallowed |
| WGK Germany | 1 |
| RTECS | NI3517000 |
| HS Code | 29332900 |
| Toxicity | LD50 in male mice, rats (mg/kg): 2629, 2854 orally (Schlüter) |
1-[P,ALPHA-DIPHENYLBENZYL]IMIDAZOLE - Nature
Open Data Verified Data
White Crystal or crystalline powder, tasteless, insoluble in water. Crystallization from acetonitrile, melting point 142 °c. Strong lipophilic. Soluble in alcohol, dimethyl formamide, dimethyl sulfoxide. pH 6 water solubility:
Last Update：2024-01-02 23:10:35
1-[P,ALPHA-DIPHENYLBENZYL]IMIDAZOLE - Preparation Method
Open Data Verified Data
a-biphenyl benzyl alcohol is added to the reaction solution, which reacts with sulfoxide chloride in acetonitrile to Form 1,1 '-sulfinyl bis (imidazole), bifonazole was obtained by reaction at room temperature.
Last Update：2022-01-01 09:08:32
1-[P,ALPHA-DIPHENYLBENZYL]IMIDAZOLE - Use
Open Data Verified Data
with broad-spectrum antifungal effect, against Candida albicans, various ringworm, yeast vaccine, filamentous bacteria and biphasic fungi, and has strong antibacterial activity. It is suitable for the treatment of fungal infections of tinea Manus, tinea pedis, Tinea corporis, tinea cruris, tinea versicolor, tinea scrotum, and skin folds.
Last Update：2022-01-01 09:08:33
1-[P,ALPHA-DIPHENYLBENZYL]IMIDAZOLE - Safety
Open Data Verified Data
male mice, rats oral LDsa:2629,2854 (mg /kg).
Last Update：2022-01-01 09:08:33
1-[P,ALPHA-DIPHENYLBENZYL]IMIDAZOLE - Reference Information
| Update Date: | 2022/11/12 10:05:38 |
| Introduction | bifonazole is an imidazole derivative with broad antibacterial spectrum, which has inhibitory effect on 90% of pathogenic fungi, can inhibit a variety of skin fungi (such as Trichophyton, Microsporum), yeast (such as Candida, yeast, smooth ball yeast), mold (such as Aspergillus) and various fungi (e. G., Coccidioides, blastomycetes, Histoplasma). |
| adverse reactions | The main adverse reactions are a small number of patients with local erythema, rash, itching, cracking, burning or tingling sensation, occasionally, contact dermatitis occurs. |
| pharmacological kinetics | after the skin was coated with 14C labeled bifonazole, the radioactivity test results of skin tissues showed: the concentration of bifonazole ranged from 1mg/cm3 in the stratum corneum of the epidermis to 5 μg/cm3 in the papillary layer of the dermis. The concentration of each layer was in the range of antifungal activity, which proved the effectiveness of this drug for external use. After fungal cell absorption, there was a high concentration of active substance in the cytoplasm after 10~30min, and it lasted for 100~120H. After the 1% bifonazole cream was used, the activity in the dermis lasted for 48h, and the blood concentration was lower than the minimum detectable concentration by HPLC. It can be seen that bifonazole cream after external use not only has high curative effect, but also has long-lasting effect, and only needs to be applied once a day in clinic. |
| pharmacological action | bifonazole has a broad spectrum of anti-dermatophytes, yeasts, filamentous bacteria and biphasic fungi, and has strong antibacterial activity. It is also effective against Malassezia furfur and gram-positive cocci. Animal Experimental dermatophytosis topical effect is good. |
| preparation | add 2000kg of imidazole, KG of 4-phenylbenzophenone, kg of potassium borohydride and 90kg of water to a liter enamel reactor, after the addition, the temperature was raised to 130 ° C., and the temperature was maintained at 130-135 ° C. For 2 hours. After the heat preservation, 40kg of ammonium bromide was added, and the temperature was raised to 195 ° C., and the reaction was maintained at 195-200 ° C. For 2 hours. After heat preservation, cooling to room temperature, add 10% of toluene Dropwise, add of hydrochloric acid Dropwise, stir for 10 minutes, let stand for stratification, adjust PH = 9 in water layer, press filtration, and recrystallize filter cake with acetonitrile, bifonazole was obtained. The yield was 80%. |
| Use | new imidazole topical antifungal agents. It is suitable for the treatment of fungal infections of tinea Manus, tinea pedis, Tinea corporis, tinea cruris, tinea versicolor, tinea scrotum, and skin folds. imidazoles are new antifungal agents for external use to treat various dermatophytes, such as Tinea corporis, tinea cruris, tinea pedis and tinea pedis. New imidazoles for external use as antifungal agents for the treatment of various dermatophytes, such as Tinea corporis, tinea cruris, tinea pedis and so on |
| production method | reaction of 13.6g of imidazole and of thionyl chloride in of acetonitrile to produce 1,1 '-sulfinyl bis (imidazole); 13g of α-biphenylbenzyl alcohol was further added to the reaction solution, and the mixture was reacted for 15h at room temperature to obtain 8.7g of bifonazole. |
| category | toxic substances |
| toxicity grade | poisoning |
| Acute toxicity | oral-rat LD50; 1463 mg/kg; Oral-mouse LD50; 2629 mg/kg |
| flammability hazard characteristics | flammability; Toxic NOx smoke from combustion |
| storage and transportation characteristics | ventilation and low temperature drying |
| fire extinguishing agent | dry powder, foam, sand, carbon dioxide, water mist |
Last Update：2024-04-09 18:58:34
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